Yarn conditioning process



STATES PATEN YARN CONDITIONING Pnoonss No Drawing; Application December 21, 1938,

Serial No. 247,104

4 Claims.

This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate, to render them more amenable to textile operations such as knitting and the like.

As is well known in the manufacture of yarns, particularly those composed of or containing cellulose organic derivatives, it is necessary to treat the yarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. It is also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly important that the yarn be soft and pliable in order that it may conformreadily to the contour of the needles and thus produce a closely knit fabric free from such defects as stitch distortion, pin holes, laddering, and the like.

Heretofore it has been proposed to employ softening agents such as polyhydrio alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found. however, that most of the known lubricating agents and thevarious formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insufficient lubricating power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas, In addition, many of the known lubricating agents or insufliciently soluble in water to permit satisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the treatment of yarnscomposed of or containing organic derivatives of cellulose and capable of lubricating, deelectriiying and otherwise rendering such yarns more amenable to knittingand other textile operations. A further and specific object is to provide a class of conditioning agents which augment or assist the lubricating action of carious lubricants when applied to such yarns.

- inorganic bases.

A still further object 'is to provide yarn lubricating formulas which can be readily removed from the yarns by the usual scour baths. A still furtlier object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate, whereby the yarn is rendered capable of employment in a variety of textile operationswhere complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including circular knitting, weaving, spinning, and particularly in the manufacture of cut staple fiber and the like. Other objects will appear hereinafter. These objects are accomplished by the following invention which, in its broader aspects, com prises the discovery that hydroxy alkane sulphonates and salts thereof derived from organic and inorganic bases and esters of hydroxy alkane sulphonates and sales derived from organic and The hydroxy alkane sulphonates and their salts may be designated {by the general formula:

The esters of hydroxy alkane sulphonates and their salts may be designated by the general for (bis 1, 2, 3, 4, 5, and 6). In the above formulae X is a substitutent selected from the group'consisting of hydrogen and salt-forming radicals; b is 1, 2, etc.; R is a substituent selected from the group consisting of the substituted and unsubstituted alkyl and cycloalkyl groups, and R is a substituent selected from the group consisting of the substituted and unsubstituted alkyl, 'alkylene, aryl, heterocyclic and cyclo alkyl groups, may be used as yarn conditioning agents and particularly as softening agents, with or without the addition of animal, mineral, or vegetable oils, in the treatment of yarns .composed or or containing organic derivatives of cellulose. l have found that these compounds when employed as described in the detailed examples set forth below have a slight solvent and/or softening action on cellulose organic derivative yarns which renders such yarns soft and pliable without at the same time having too drastic an action thereon.

The intermediate necessary for the preparation of these compounds are prepared by treating alkylene oxides (ethylene, trimethylene, propylkit with various hydrosulfide salts (sodium, potassium, ammonium, etc.) by methods previously described. Compounds of the type:

where X is ammonium, metal, etc., are formed. These compounds are then esterified by treating with organic acid anhydrides, chlorides, acids, etc. In addition I may prepare compounds of this type by treating halogenated alkyl sulfonates and their salts with salts of organic acids using known methods. I

Examples of the preparation of typical compounds ofthis type are as follows:

PREPARATION or Esraas Example 1 14.8 gm. sodium-p-hydroxyethane sulfonate having the formula HOCHr-CH5S-ON&

are placed in acetic acid and treated at 60 with 105 gm. acetic anhydride. Heating is continued for several hours and. then the acetic acid is removed from the sodium-p-hydroxyethane sulphonate acetate having the formula CHr-8-OCH:CHr-SON3 under reduced pressure. In a similar manner I may prepare the propionate, butyrate, valerate, laurate, oleate, stearate, etc.

Emample 2 177 gm. potassium-fi-hydroxypropane sulfonate having the formula CHa-CH-CHrS-OK (gammahydroxy-delta-hexane sulionic acid ammonium salt) are dissolved in acetic acid and treated with 550 gm. oleic anhydride as described in Example 1. The ester which is the oleate of gamma-hydroxydelta-hexane sulfonic acid ammonium salt has the formula:

In a similar manner the crotonate, cinnamate, etc. may beprepared.

. Eaample 4 202 gm.

mc-om H (Sodium-241ydroxycyclohexane sulfonate) is filtered off and the reaction product is worked up as described in Example 1.

Example 5 14.2 gm. fi-v-dihydroxypropane sulfonate having the formula are placed in an esterification apparatus with benzene, hexahydrobenzoic acid. The dihexahydrobcnzoate having the formula l l oH=-oH, co co carom on, on o11 on,

carom om-on,

is formed by distilling off the water using p-toluene-sulfonic acid as a catalyst. In a similar manner there may be prepared the naphthenate abeitate, succinate, etc.

In accordance with the invention these compounds may be applied directly to the yarn during or after spinning, or may be added to the spinning solution itself. I have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they may be, and preferably are, employed as ingredients of yarn conditioning or lubricating formulas in conjunction with agents which function wholly or partially as lubricants.

I have also found that the above mentioned compounds are particularly valuable as antistatic agents when applied to filaments, threads, fabrics, etc., composed of or containing organic derivatives of cellulose, such as cellulose acetate, cellulose propionate, cellulose acetate butyrate, and the like, and to textile materials in general.

In the folowing examples and description I have set forth several of the preferred embodiments of my invention, but they are included merely for purposes of illustration and not as a limitation thereof.

My invention will be more readily understood by reference to the following examples in which typical applications of the invention are. set forth.

Example 5 is applied to textile materials (silk, cotton, wool. viscose, cellulose acetate, etc.) by means of a bath, wick, roller, spray, etc. to iacilitate their knitting, weaving, spinning and the like. Yarns lubricated with this compound are of special value in the preparation of cut staple fibers. In place of the ammonium salt there may be used the salt of any. primary, secondary, tertiary or quaternary amine such as ethanol-, triethanol-, oleyl-, dio1eyl-. tributyl-, morpholine, cyclohexyl-, ditetrahydroiurfuryl-, etc.

Example 7 A conditioning liquid is made up as follows: Sodium ,6, -dihydroxy butane acetate stearate having the formula I O 0 CO C0 1-20 parts, and glycerol acetone butyrate, 99-80 parts. This is applied to textile materials such as silk, wool, cellulose acetate, etc. as described in Example 6. If the yarn is intended primarily for knitting, the amount of conditioning liquid applied may vary from 425% by weight of the yarn and if for weaving between 1-5% by weight of the yarn.

Cellulose acetate filaments treated as described are quite soft and pliable and give improved results in various textile operations such as weaving, knitting, etc. and especially in the production of cut staple fibers.

Other examples of yarn conditioning compositions which may be applied to varioustypes of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with my invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are as follows:

Example 8 Parts Sodium-fi'hydrcxyethane sullonate acetate Example 11 OKs-CH9 SOr-H(N-OsHcOH)I Part1 C\ G 1-10 CHr-O CHIP-CH:

O-G- H H: 1 0

(Trlethanolemine salt of Z-hydroxycyclohexanc sullonatc tetrahydroiuroate) Blown host's-foot oil W-OO Example 12 Sperm oil..' 98

I 1 0 C H11-Cc B0|HN-C|Hu 2 o-on,-0om (Monodecane-(i-hydroxy (methcxyacetatc)-7-sul1onatc cyclohexylamine salt) Example 13 Blown s perm oil Stearate o1 B-hydroxyethane sulionate benzylamine salt onnu-o-oclnr-s-onnmomo Example 14 MineraioiL Napllgthenate o1 B-hydroxyethane sullonate 'cyclohexylamine Nphthenyl-O-O-CaHE-S-0H.NH C Hn ll O 0 5-1 Example 15 Teaseed oil 5,fi-Tetrahydroiurfurylethylether 25 Snccinate oi fl-hydroxy propyl 511110 to trimethyl benzyl ammonium hydroxide salt"..

on; on, HC-Q ('TC:H(3-0--4|JH HI 0 CH1 b=S=O O=IS-OH.HOII-I(CH;)!

( JH.HO.N(CH:)E l

Example 16 -Water Gelatin s 10 Tetrahydrofurfuryl tetrahydroluroate 5 /CHr-CE CQH11-CO-GH-CHFSO3H1HN /0 o omon car-on,

(Bpta-hexahydrobenzoate of lbeta-l dihydroxypropane sulfonate morphollne salt) Example 17 l 5 0 0 I 0 O 0 (30 #0 (2, 3-dihydroxy butane-l, 4-sulionate sodium'ammonluni salt acetate 'benzoate) Example 18 Crglitonate of fi-hydroxy butane sulionate ethylene, diamine s CHr-CHzCH-CH:S-OH.NHzCgHr-NHQ CC=C-CH| O H H Blown olive oil 9a Example 19 Parts B-Hydroxy pentane sulfonate (CHz-(CHa)rC H-CHz- S OH) 1 H 0 e, Stearate pentane sulfonate CHs-(CH2)zCHCH:S-OH

0CC11H Oleic acid 5 Olive oil 90 Example 20 Sodium sulfate 2 Stearate of B-bydroxyethane sulionate sodium salt CHa-(CHz):CHCH:S-O Na O-COC 7Hu 3 Blown olive oil 80 Sulioneted castor oil 10 Oleic acid 5 Example 21 In a 20 percent acetone solution of cellulose acetate are dissolved 1-5% by Weight of one or more of the compounds claimed in this application. The acetone solution is then extruded into an evaporative atmosphere and the filaments thus produced are wound or twisted and .wound. If desired, the filaments produced by this process areoiled with any of the combinations of lubricants or lubricants plus conditioning agents previously described. Filaments thusprepared are of particular value in the preparation of cut staple fibers.

Any of the above compositions may be applied to the yarn intended for use in circular knitting by means of a bath, wick, spray, roller, pad or any suitable means. The amount of conditioning liquid applied may vary between 5-25% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about 10-15% by weight of the yarn, Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.

As will be apparent from the above examples and description the conditioning agents of my invention may be applied by a wide variety of methods. For example, I may employ the agent as an ingredient of the spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, such as the particular cellulose derivative used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

If the conditioning a.gent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll, or felt wet therewith, or the liquid may be appliedby immersion, spray, or otherwise. The particular point at which the liquid is applied may vary. It may, for example, be applied to the yarn inside or outside the spinning cabinet; between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by the so-called bobbin to bobbin" method. 7

In the case of staple fiber manufacture, 'the liquid may be applied to the yarn prior to, or after cutting into staple lengths.

The amount of theagent so employed will vary widely depending upon the results desired, the specific nature of the material to which the agent is applied, the use to which the yarn is eventually to be put and other factors. For example, in a given case where a cellulose organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.

Although in the above examples I have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending agents and the like, may be added within the scope of my invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although I have found it convenient to illustrate my invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted, as, for example, by reducing the amount of the agent and correspondingly increasing the amount of oil or other ingredient.

While I have described my invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl celluloseand others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials. j

The term yarn as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

As indicated above, the yarn conditioning agents of my invention. are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neatsfoot, sperm and other oils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying composition.

The yarnconditioning method and compositions of my invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to deelectrify yarns, especially those composed of or contaning organic derivatives of cellulose such as celluloseacetate and render them amenable to various textile operations, especially the manufacture of cut staple fiber. Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils-and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of my invention as herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.

What I claim is:

l. The process of conditioning yarn composed of or containing organic derivatives of cellulose to render it amenable to textile operations, including knitting, weaving, spinning, and the manufacture and use of staple fibers, which comprises applying to the. yarn a lubricating and antistatic composition containing as its essential lubricating and anti-static component a compound selected from the group consisting of the hy- 'droxy alkane sulfonates and the salts thereof derived from organic and inorganic bases and the esters thereof.

2. The process of conditioning yarn composed of or containing cellulose acetate to render it amenable to textile operations, including knitting, weaving, spinning, and the manufacture and use of staple fibers, which comprises applying to the yarn a lubricating and anti-static composition containing as it essential lubricating and anti-static component a compound selected from the group consisting of the hydroxy alkane sulfonates and the salts thereof derived from organic and inorganic bases and the esters thereof.

3. Textile yarns composed of or containing organic derivatives of cellulose, amenable to textile operations, including knitting, weaving, spinning, and the manufacture of staple fibers, said yarns being impregnated'with a lubricating and anti-static agent comprising a compound selected from the group consisting of the hydroxy alkane sulfonates and the salts thereof derived from organic and inorganic bases and the esters thereof.

4. Textile yarns composed of or containing cellulose acetate amenable to textile operations, including knitting, weaving, spinning, and the manufacture of staple fibers, said yarns being impregnated with a lubricating and anti-static agent comprising a compound selected from the group consisting of the hydroxy alkane sulfonates and the salts thereof derived from organic and inorganic bases and the esters thereof. ,1

JOSEPH B. DICKEY. 

